allyl-O-<3-O-(4-methoxybenzyl)-β-D-galactopyranosyl>-(1->4)-β-D-glucopyranoside | 227601-47-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl-O-<3-O-(4-methoxybenzyl)-β-D-galactopyranosyl>-(1->4)-β-D-glucopyranoside
• 英文别名: allyl 3-O-(4-methoxybenzyl)-β-D-galactopyranosyl-(1,4)-β-D-glucopyranoside；Mob(-3)Gal(b1-4)Glc(b)-O-allyl；(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-prop-2-enoxyoxan-3-yl]oxy-6-(hydroxymethyl)-4-[(4-methoxyphenyl)methoxy]oxane-3,5-diol
• CAS: 227601-47-0
• 化学式: C₂₃H₃₄O₁₂
• 分子量: 502.516
• InChiKey: DMVHPNGJCCUAJC-JARVZVEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  177
• 氢给体数：
  6
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  allyl-O-<3-O-(4-methoxybenzyl)-β-D-galactopyranosyl>-(1->4)-β-D-glucopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 allyl 2-O-benzoyl-4,6-O-benzylidene-3-O-(4-methoxybenzyl)-β-D-galactopyranosyl-(1,4)-2,3,6-O-tri-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  Thio-isoglobotrihexosylceramide, an Agonist for Activating Invariant Natural Killer T Cells

  摘要：

  Thio-isoglobotrihexosylceramide (S-iGb3) might be resistant to alpha-galactosidases in antigen-presenting cells and have a longer retaining time in the lysosome before being loaded to CD1d. The biological assay showed that S-iGb3 demonstrates a much higher increase as a stimulatory ligand toward invariant natural killer T (iNKT) cells as compared to iGb3.

  DOI：

  10.1021/ol062199b
• 作为产物：
  描述：

  2,2',3,3',4',6,6'-七-O-乙酰基-alpha-D-乳糖基溴化物 在 甲醇 、 四丁基溴化铵 、 sodium methylate 、 氰化汞 、 二正丁基氧化锡 作用下， 反应 49.75h， 生成 allyl-O-<3-O-(4-methoxybenzyl)-β-D-galactopyranosyl>-(1->4)-β-D-glucopyranoside
  参考文献：
  名称：

  Kononov; Kornilov; Sherman, Russian Journal of Bioorganic Chemistry, 1998, vol. 24, # 8, p. 537 - 550

  摘要：

  DOI：

文献信息

• Potential use of synthetic α-galactosyl-containing glycotopes of the parasite Trypanosoma cruzi as diagnostic antigens for Chagas disease
  作者：Roger A. Ashmus、Nathaniel S. Schocker、Yanira Cordero-Mendoza、Alexandre F. Marques、Erika Y. Monroy、Andrew Pardo、Luis Izquierdo、Montserrat Gállego、Joaquim Gascon、Igor C. Almeida、Katja Michael

  DOI：10.1039/c3ob40887f

  日期：——

  A synthetic glycoarray containing non-reducing α-galactopyranosyl moieties related to mucin O-glycans of the parasite Trypanosoma cruzi was evaluated by a chemiluminescent enzyme-linked immunosorbent assay with sera from patients with chronic Chagas disease. Our data revealed the disaccharide Galα(1,3)Galβ as the immunodominant glycotope, which may eventually be employed as a diagnostic antigen for Chagas disease.

  合成糖阵列含有与寄生虫克氏锥虫粘蛋白 O 聚糖相关的非还原性 α-吡喃半乳糖基部分，通过化学发光酶联免疫吸附测定对慢性恰加斯病患者的血清进行评估。我们的数据显示二糖 Galα(1,3)Galβ 作为免疫显性糖表位，最终可能用作恰加斯病的诊断抗原。
• Study of glycosylation with N-trichloroacetyl-d-glucosamine derivatives in the syntheses of the spacer-armed pentasaccharides sialyl lacto-N-neotetraose and sialyl lacto-N-tetraose, their fragments, and analogues
  作者：Andrei A. Sherman、Olga N. Yudina、Yury V. Mironov、Elena V. Sukhova、Alexander S. Shashkov、Vladimir M. Menshov、Nikolay E. Nifantiev

  DOI：10.1016/s0008-6215(01)00213-0

  日期：2001.11

  The syntheses of 2-aminoethyl glycosides of the pentasaccharides Neu5Ac-alpha (2 --> 3)-Gal-beta (3(1 --> 4)-GlcNAc-beta (3(1 --> 3)-Gal-beta (1 --> 4)-Glc and Neu5Ac-alpha (2 --> 3)-Gal-beta (1 --> 3)-GlcNAc-beta (1 --> 3)-Gal-beta (1 --> 4)-Glc, their asialo di-, tri-, and tetrasaccharide fragments, and analogues included a systematic study of glycosylation with variously protected mono- and disaccharide donors derived from N-trichloroacetyl-D-glucosamine of galactose, lactose, and lactosamine glycosyl acceptors bearing benzoyl protection around the OH group to be glycosylated. Despite the. low reactivity of these acceptors, stereo specificity and good to excellent yields were obtained with NIS-TfOH-activated thioglycoside donors of such type, or with AgOTf-activated glycosyl bromides, while other promotors, as well as a trichloroacetimidate donor, were less effective, and a beta -acetate donor was inactive. In NIS-TfOH-promoted glycosylation with the thioglycosides, the use of TfOH in catalytic amount led to rapid formation of the corresponding oxazoline, but the quantity of TfOH necessary for further efficient coupling with an acceptor depended on the reactivity of the donor, varying from 0.07 equiv for a 3,6-di-O-benzylated monosaccharide derivative to 2.1 equiv for a peracetylated disaccharide one. In the glycosylation products, the N-trichloroacetyl group was easily converted into N-acetyl by alkaline hydrolysis followed by N-acetylation. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Kononov; Kornilov; Sherman, Russian Journal of Bioorganic Chemistry, 1998, vol. 24, # 8, p. 537 - 550
  作者：Kononov、Kornilov、Sherman、Zyryanov、Zatonsky、Shashkov、Nifant'ev

  DOI：——

  日期：——
• Thio-isoglobotrihexosylceramide, an Agonist for Activating Invariant Natural Killer T Cells
  作者：Chengfeng Xia、Dapeng Zhou、Chengwen Liu、Yanyan Lou、Qingjia Yao、Wenpeng Zhang、Peng George Wang

  DOI：10.1021/ol062199b

  日期：2006.11.1

  Thio-isoglobotrihexosylceramide (S-iGb3) might be resistant to alpha-galactosidases in antigen-presenting cells and have a longer retaining time in the lysosome before being loaded to CD1d. The biological assay showed that S-iGb3 demonstrates a much higher increase as a stimulatory ligand toward invariant natural killer T (iNKT) cells as compared to iGb3.